Turning Travel Problems into Travel Opportunities in Chicago

Chicago is a city that’s been on my radar for quite some time, but never enough to actually motivate a visit. I figured I’d go someday, but not quite yet!

I unexpectedly visited a few weeks ago when my flight from Montreal to Chicago was delayed. As soon as I realized I was going to miss my connection into Shanghai, I started trying to figure out how I could finagle a night in Chicago – something that would actually be more convenient for my schedule. After three hours of negotiating and trying to explain that I actually wanted to be in Beijing the NEXT day, the fourth employee I talked to booked me on a flight the next day and gave me hotel and meal vouchers for the night! I had successfully turned a missed flight fiasco into a free stay in the Windy City. Turning travel problems into travel opportunities is a great way to see new places!

I made my way to my sketchy airport hotel on a half torn-up highway and dashed into the city on the L train, determined to make the most of my few daylight hours in Chicago.

For this compulsive planner, seeing a city without having done ANY research was rather panic-inducing – Where do I eat?! How do I get around?! What do I even want to see?! However, I managed to have a great, albeit cold, time wandering downtown Chicago by myself. I think some sort of fashion event was happening that night, which meant that Millennium Park was pretty crowded with very trendy people.

I must say, the city took me by surprise. I wasn’t expecting it to feel so much like New York, and I certainly wasn’t expecting to love it so much! I could have spent forever walking around and looking up at the skyscrapers, but unfortunately I only had a few hours.

Given more time (and some more research) I would have rented a bike and explored the waterfront and tried the famous deep-dish pizza, among other things. As it was, I walked along the Magnificent Mile, through Millennium Park, and then went up the Willis Tower (formerly the Sears Tower). I had failed to bring a jacket, so I was freezing the whole time – but that didn’t stop me from enjoying myself!

The only thing on my must-see list was the Cloudgate sculpture in Millennium Park, since I had seen countless pictures on travel blogs. It was just as cool as it seems; this superbly reflective sculpture was very crowded and I see why!

After getting a nice solo French girl to take my picture (see above) and walking under the sculpture to admire the crazy distortions, I proceeded to wander around the rest of the park. I also tried to get onto the waterfront, but due to my lack of research I ended up in a construction zone!

Luckily, my random vantage point allowed me some breathtaking views of the city. The clouds looked surreal and I unabashedly stood on a bench to get these pictures.

My parents suggested that I go up the Willis Tower ($19), so I made my way to America’s tallest tower based on the terrible tourist map I found at the hotel. The staff said the wait to go up the tower would be about an hour and a half, but as it was getting dark I didn’t mind being inside for a while! Once I made my way through the endless lines and security checks, we were treated to a short video on the history of the tower. Sounds boring, right? It was actually fascinating, and the graphic design was very well done!

Since it had been such a nice day, the tower was insanely crowded. It was nice to be solo, since I could more easily squeeze in front of people! The tower features several alcoves with glass floors, as well as tons of windows on all the sides of the building. I took approximately 10,000 pictures from each angle – I’m a sucker for a good nighttime city view.

I had no desire to wander alone in Chicago at night, so once I was done admiring the view, I tried to find my way to the nearest train stop. This took much longer than it should have, and I kept going in circles around the tower! At some point someone asked me for directions, which I found hilarious since I was lost. Needless to say, I couldn’t help them!

Eventually I succeeded, and hopped back on the train to the Holiday Inn O’Hare. The next morning I boarded a 14 hour flight, pleased that I had negotiated my way into seeing this city! I already want to go back – this time with more time and a solid plan.

Have you ever turned a travel problem into a travel opportunity? How do you deal with not knowing anything about a city?